title: N-Heterocyclic carbene-catalyzed (4+2) cycloaddition/decarboxylation of silyl dienol ethers with α,β-unsaturated acid fluorides.
abstract: Herein we report the first all-carbon N-heterocyclic carbene-catalyzed (4 + 2) cycloaddition. The reaction proceeds with α,β-unsaturated acid fluorides and silyl dienol ethers and produces 1,3-cyclohexadienes with complete diastereocontrol (dr >20:1) while demonstrating a new type of reaction cascade exploiting α,β-unsaturated acyl azoliums.
authors.affiliation: School of Chemistry, Monash University, Clayton 3800, Victoria, Australia.
authors.forename: Sarah J
authors.initials: SJ
authors.lastname: Ryan
authors.forename: Lisa
authors.initials: L
authors.lastname: Candish
authors.forename: David W
authors.initials: DW
authors.lastname: Lupton
mesh_terms: D000143:Acids / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D053138:Cyclohexenes / Q000138:chemical synthesis / Q000737:chemistry; D003653:Decarboxylation; D004987:Ethers / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000143:Acids; D053138:Cyclohexenes; D004987:Ethers; D006571:Heterocyclic Compounds; D006845:Hydrocarbons, Fluorinated; C030011:carbene; C034005:1,3-cyclohexadiene; D008697:Methane